Sodium Chlorite → 3-Fluoro-2-hydroxy-4-methoxybenzoic acid

HRID 629478Notes

Reaction equation

HRID 629478 reaction equation
[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[CH:5]=[O:6].P([O-])(O)(O)=[O:14].[Na+].Cl([O-])=O.[Na+]>CS(C)=O.O>[F:1][C:2]1[C:3]([OH:12])=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH3:11])[C:5]([OH:14])=[O:6]

Participants

6

Reactant 3

HCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 847318613-Fluoro-2-hydroxy-4-methoxybenzaldehyde

Product 1

HCID 847699353-Fluoro-2-hydroxy-4-methoxybenzoic acidYield 67.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

To a mixture of 3-fluoro-2-hydroxy-4-methoxybenzaldehyde (10.0 g) and sodium dihydrogenphosphate (22.9 g) in DMSO (100 mL) and water (25.0 mL) was added dropwise an aqueous solution (30.0 mL) of sodium chlorite (14.5 g), and the mixture was stirred at 20° C. for 16 hr. The solvent was evaporated under reduced pressure, the residue was diluted with water, and the mixture was extracted with ethyl acetate (×6). The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (7.42 g).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe mixture was extracted with ethyl acetate (×6)
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-f03d44b911bd43ecab8cc987be2239d9
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Reaction notes

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